Water → Ethyl 5-chloro-3-hydroxy-1-benzofuran-2-carboxylate

HRID 259282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 259282
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[C:14](OCC)=[O:15])[CH3:2].O>C(O)C>[C:4]([C:5]1[O:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[C:14]=1[OH:15])([O:3][CH2:1][CH3:2])=[O:19]

Komponenten

4

Edukt 2

HCID 962WaterHCID 306038Ethyl 5-chloro-2-(ethoxycarbonylmethoxy)benzoate

Produkt 1

HCID 54723611Ethyl 5-chloro-3-hydroxy-1-benzofuran-2-carboxylateAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

12.3 g (0.11 mol) of potassium tert.-butylate were added in portions to a solution of 28.6 g (0.1 mol) of (2-carbethoxy-4-chlorophenoxy)-acetic acid ethyl ester in 50 ml of ethanol. The batch was warmed to 80° C. for 2 hours and was then cooled, and the reaction mixture was poured into 200 ml of water. The aqueous solution was first extracted with methylene chloride (to remove neutral impurities) and was then acidified with hydrochloric acid while cooling with ice. The acid solution was repeatedly extracted with methylene chloride. The combined organic extracts were dried over sodium sulfate and then concentrated. 21 g (87.5% of theory) of 2-carbethoxy-5-chloro-3-hydroxy-benzofuran were obtained in the form of colorless crystals of melting point 100°-102° C.

Aufarbeitung

  1. temperaturewas then cooled
  2. extractionThe aqueous solution was first extracted with methylene chloride (to remove neutral impurities)
  3. temperaturewhile cooling with ice
  4. extractionThe acid solution was repeatedly extracted with methylene chloride
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0bbd08f1b1e4277a113f9d21037b34d
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04036982

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